of basel



Patented Mar. 5, 1929. i

UNITED STATES PATENT OFFICE.

FRITZ STBAUIB, OI BASED, SWITZERLAND, ASSIGNOR TO THE SOCIETY 01 CHEMICAL INDUSTRY IN BASLE, OF BASED, SWITZERLAND.

PROCESS FOR THE PRODUCTION OF FAQ! TINTS 0N VEGETABLE FIBER.

No Drawing. Application filed May 23, 1927, Serial No. 193,730, and in Switzerland May 27, 1926.

The present invention relates to a process for producing fast tints on vegetable fibers. It comprises the process for producing these fast tints, and the material that has been dyed accordin to this new process.

It has been iiound that the chromium compounds of azo-dyestuifs from diazo-co1npounds which contain in ortho-position to the diazo-group a group adapted to form lakes, such as the OH-group, or the carboxyl group,

- and which hitherto have been used chiefly for dyeing animal fibers, are, also suitable for producing fast tints on vegetable fibers. This result could not be anticipated and is the more surprising, because when wool dyed with chromium compounds is subjected to alkaline fulling in presence of cotton, the latter does not become dyed.

The fulling of wool consists, as is wellknown, in treating this material at about C. for a long time in a fulling machine with a fullin liquid containing soap and soda. During t is operation there is always passing some dyestufi from the wool -fiber into the fulling liquid. Now, if wool, as is frequently the case, is fulled in presence of cotton, then cotton is dyed by the dyestuil which is contained in the alkaline fulling liquid, if this dyestufi' has aflinity for cotton. It is there-.

fore to be considered as altogether surprising that when wool dyed with chromium compounds of ortho-hydroxy-azo-dyestufis or ortho-carboxy-a-zodyestuffs is fulled in presence of cotton the latter is not dyed, although it can be smoothly dyed under the conditions of a dyeing bath.

The dyeings produced on vegetable fibers by means of chromium compounds of orthohydroxy-azo-dyestuffs or ortho-carboxy-azodyestuffs may be distinguished by their very good fastness to light, and by their remarkable fastness to water and washing surprising for direct 'cotton dyestuffs which, generally, do not possess these properties.

The aflinity of the chromium compounds of certain azo-dyestuflis is particularly good for vegetable fibers, namely whenthe 'dyestufiz' is derived from such components as lend to the azo-dyestufif made from them an aflinity for cotton. Such components are, among others, the 2:5:7-, the 2:8:6- and the 125:7- amino-naphtholsulfonic acids and the derivatives and substitution products thereof; further the products which contain the residue of the (lehydrothio-p-toluidine, ofthe primuline, and the like, are particularly suitable. Such products are, for example, the dyestuffs which are obtained from the condensation products of (lehydrothiotoluidine or of primuline with acetoace-tic ester and orthohydroxy-diazo-compounds.

The following example illustrates the in vention, the parts being by weight Emample.

A 'dye bath is prepared with 2 parts of the chromium compound of the azo-dyestuif from diazotized 2-amino-4-chloro-5-nitro-1-phenol and 2 5-aminonaphthol-7 sulfonic acid (acid coupling) corresponding with the formula HO NH:

.may also be conducted in a weakly alkaline or weakly acid bath, if necessary with addition of chromium salts.

The following table gives a range of tints which can be obtained according to the new process Diazotizing Tint of the direct component .Couplmg component cotton dyeing 2 amino 1 phenol 4 Aeetoacetic anilide.- Greenish yellow.

sulfo' 6 earboxylie acid. 2 -amino-l-plienol-4- Aeetoeeetie a naphsulfo 6 earboxylic thylsmide.

Acetoaeetic p dichloro-anilide.

acid.

2 amino 1 phenol g Greenisli -yellow.

sullo 6 carboxylic acid.

2-amino-1-phenol-4- Aeetoacetic o toluisulfo 6 carbo dide.

Greenish yellow. xylic acid. 2-amino-1-phenol-4- Aeetoaeetlc o anisisulfo 6 carboxylic dide.

acid. l-aminobenzene-z-mb Aeetoaeetlc anilide boxyllc acid.

Yellow.

Greenish yellow Greenish yellow.

l-phenol.

2-amino-1 -phenol-4- sullo 6 carboxylic acid.

coup g). 2-amlno-1-phencl-4- aullamide.

Nltrated dlazo com- 5:5 dioxy 7:7 disull'onic acid.

Secondary condensation product from 1 mol. 1:8-aminonaphthol 3:6 disulfonic acid. 1 mol. cyanuric chloride and 1 mol. aniline.

2:5 aminonaphthol 7 sullonic acid.

1:5-dloxynaphthalin 5:8 dichloro 1 naphlfllol.

2:5 amlnonaphthol 7 sulfonic acid.

Sulfonic acid of the 2:4- diamino 4.- chlorodiphenyl eth 4 Greenish tinged Gray.

Gray.

Gray.

Reddish gray.

Brown.

Diazotizing I Tint of the direct Dinzotizing Tint of the direct component coupl'ng component cotton dyeing component C HDII E component cotton dyeing 2 amino 1 phenol -4- Acetoacetic este Yellow. 2 amino l -phenol 4 2:4 diaminodiphenyl Brown.

sulfonic acid. sullonic acid. 4 other.

2 amino 1 phenol 4 Acetoacetic ester Yellow. 2 amino 1 phenol 4 m-phenylendiaminc Brown.

chloro-5-sullonic acid. sulfonic acid.

4-nitro-2-amino-l-phenol Aoeooacetic ester- Yellow. Nltrated diazo corn- Acetoacetic-o-xylidide. Brown.

4 chloro 2 amino 1 Acetoaoctic enilid Yellow. pound of the 1:2-amiphenol-o-sulfonic acid. nonaphthol+sulfonie 4 nitro 2 amino 1 Acetoacetic anilide.. Yellow. acid.

phenol-esullonic acid. Nitrated diazo com- Acetoacctico-tolnidide. Brown.

2 amino 1 phenol -4 Aoetoaoetic p chloro- Yellow. pound of the 1:2-amisulgo 6 carboxylic anilide. nopiaphthoH-sullonic 8C1 ac! 4 nitro 2 amino 1 Aeetoace'tic anilide.'.... Yellow. 2 amino 1 phenol -4 4 chloro 1:3 phenyl Brown.

phenol 6 carboxylic sulfonic acid. endiamine. acid. 2 amino 1 phenol 4 m-toluylendiarnine. Red-brown.

2 amino- 1 phenol 4 Acetoacetic p chlor0- Yellow. ulfonic acid.

sullonic acid: anilide. ltrated diazo com- Aeetoacetic o chloro- Red-brown.

2- amino 1 -phenol 4 Acetoacetic o tolui- A red yellow. pound of the 1:2-amianilidc.

sulfonic acid. didc. nonaphthol-4-sullonic 2 amino l phenol-4- Acctoacetic-o-xylidide A red yellow. acid.

chloro-Mulfonic acid. -Nitratcd diazo com- Acctoacetic-m-xylididc. Rod-brown.

2- amino; 1 p n l-4 Acetoacetic ester A red yellow. pound of the 1:2-amichloro-5-sullonic acid. nonaphthoH-sulfonic 2-amino-4-acetylamin9- Acetoaceticanihde. A red yellow. acid.

1 phenol 6 sultonic 2- 81111110 l phenol 4 2:4 diammodiphenyl Red-brown. acid. sulfamide. ether 4 sulfonic 2-amino 1 -pheno l -4 Acetoacetic m tolui- A red yellow. acid.

chloro-fi-sulfonic acid. dide.

zino- 1 1dJhenol-4- Ageltzioacetic o anisi- A red yellow.

S 01110801 l e.

2-atl nimi-54-l-llfiethyl-l Aoetoacetic anilide-...- Ared yellow. I claim f f v p 8110- S 01110 801 l 2-a1nino-1-phenol-4- Acetoacetic ester.-. A red yellow. recess or t m producfilop 0 i chloro-o-sull'glnic l ng. to] l on the vegetable fiber, consisting 1n dyeing -amino- -p eno -s ami o -p erange. 1

sulmmide 3 5 I w 10 1 a\ e een prepared with Clll om 1un1 m 1 pyrzilzololipf. Red compounds of azo-dyestuffs from such (haze 'gfifif' fi, compounds wh1ch contain 1n the ortho-posig gi fi g g 5 Mon to the d1azo group a group adapted to the lmmminonaighhol the oi lgm-an iimp- Pink. formation of lakes.

eme y 1 End? ac 1 giggg olopeqlmgli). F k 2. Process for the production of fast tints Z -ammonap 0 III-811M -p 911 1n Home acid (2 mm 3 methyl 5 Pym on the vegetable fiber, conslstmg n dyeing 2 i s). 1 hm] 4 1 1 aphthalm Red violet the vegetable fiber from such dyeing baths 2 Hom mifi 1 4 1 ig ngii 1m B1 1 t whlch have been prepared with chroimum -amino- -p eno y roxynap a 6-, ue-vioe cmomssulronic acid. whenylketom compounds of azo dyestuffs from ortho 11y lzz i miponaghthol-b a-naphthol. Ared blue. droxy-dlazo compounds.

8 on 080]. 2-?flnpnoa1-phelppl-14i- Primaryctopndenlsatioii Blue. 3. Process for the productlon of fast tmts so- -carxyc rou rom mo. mm {i wulinommhthob on the vegetable fiber, conslstlng n dyemg g glf g g fg the vegetable fiber from such dyemg baths chloride. whlch have been prepared with chromium 2 amino 5 nitro 1 2:5-aminonaphthol-7- G een, i phmL Home acid (acid droxy dlazo compounds and such couphng 1 ug r mm] 6 or components which impart affimty to cotton to g g gg 41mmi fi g g gl g g Olive- 4. Process for the production of fast tints 4:6-dichloio-2-amino- 22' -dinaphthylamin- Blue-gray. on the vegetable fiber, consisting in dyeing compounds of azo-dyestufl's from ortho-hy- 10. The material dyed according to claim 4.

droxy-diazo compounds and N-aryl substi- 11. The material dyed according to claim 5.

tution products of the 2: 5-aminonaphthol-7- 12. The material dyed according to claim 6. 10

In Witness whereof I have hereunto signed sulfonic acid.

this 12th day of May 1927.

Q 5 7. The material dyed according to claim 1. my name 8. The material dyed according to claim 2. 9. The material dyed according to claim 3. FRITZ STRAUBJ 

